SET-promoted photoaddition reactions of N-α-trimethylsilylmethyl-N,N-dibenzylamines with fullerene C60. Electronic factors that govern photoaddition efficiencies

Suk Hyun Lim, Jinju Yi, Choon Sup Ra, Keepyung Nahm, Dae Won Cho, Ga Ye Lee, Jinheung Kim, Ung Chan Yoon, Patrick S. Mariano

Research output: Contribution to journalArticlepeer-review

10 Scopus citations

Abstract

Single electron transfer (SET) promoted photoaddition reactions of N-α-trimethylsilylmethyl-N,N-dibenzylamines to fullerene C60 were investigated as part of an effort aimed at developing a general method to prepare various aryl ring containing aminomethylfullerenes and exploring factors that govern photoaddition efficiencies. The results show that the photoaddition reactions take place highly efficiently to form 1,2-adducts. The mechanism for this process involves generation of aminium radicals and C60 anion radical intermediates by a pathway initiated by excited state SET. SET is followed by desilylation of the aminium radicals to produce α-amino radicals that couple with either C60 or its radical anion to form precursors of the 1,2-adducts. The electronic nature of para-substituents on the aryl ring of N-α-trimethylsilylmethyl-N,N-dibenzylamines has a pronounced effect on the efficiency of the photoaddition reaction, with electron donating groups causing a greater than 2-fold enhancement compared to that brought about by electron withdrawing groups.

Original languageEnglish
Pages (from-to)3014-3018
Number of pages5
JournalTetrahedron Letters
Volume56
Issue number23
DOIs
StatePublished - 3 Jun 2015

Keywords

  • Fullerene
  • Ion-radicals
  • SET-photochemistry
  • α-Silylamines

Fingerprint

Dive into the research topics of 'SET-promoted photoaddition reactions of N-α-trimethylsilylmethyl-N,N-dibenzylamines with fullerene C60. Electronic factors that govern photoaddition efficiencies'. Together they form a unique fingerprint.

Cite this